| Regular Article |
|
|
|
|
|
Cipatrijugin G,a new trijugin-type limonoid bearing an uncommon γ-hydroxybutenolide unit from the aerial parts of Cipadessa cinerascens |
| Cheng-Shi JIANGa, Yan LIa, Zhen-Zhong WANGb, Xiao-Yin HUANGa, Wei XIAOb, Yue-Wei GUOa |
a State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China;
b Jiangsu Kanion Pharmaceutical Co. Ltd., Lianyungang 222001, China |
|
|
|
|
Abstract A new trijugin-type limonoid, cipatrijugin G (1), together with the related known cipatrijugin A (2), were isolated from the aerial parts of Cipadessa cinerascens. The structure of the new compound was determined by extensive analysis of its spectroscopic data and by comparison of its NMR data with those reported in the literature. Compound 1 showed cytotoxicity against tumor cell line A549 with an IC50 value of 9.78 μM. This is the first report of a trijugin-type limonoid bearing a γ-hydroxybutenolide unit, in comparison to the common furan unit as ring E.
|
| Keywords
Cipadessa cinerascens
trijugin-type
limonoid
|
| Fund:This research work was financially supported by the National Marine ‘863’ Projects (No. 2013AA092902), the Natural Science Foundation of China (Nos. 21021063, 81273430, and 2107224), and was partially funded by the EU 7th Framework Programme-IRSES Project (No. 246987). |
|
Issue Date: 11 February 2018
|
|
|
| [1] |
Tan, Q. G.; Luo, X. D. Chem. Rev. 2011, 111, 7437-7522.
|
| [2] |
Yin, S.; Wang, X. N.; Fan, C. Q.; Liao, S. G.; Yue, J. M. Org. Lett. 2007, 9, 2353-2356
|
| [3] |
Mulholland, D. A.; Parel, B.; Coombes, P. H. Curr. Org. Chem. 2000, 4, 1011-1054.
|
| [4] |
Taylor, D. A. H. In Progress in the Chemistry of Organic Natural Products, ed. W. Herz, H. Grisebachand G. W. Kirby, Springer, New York, 1984, Vol. 45, pp. 1-102;
|
| [5] |
Corey, E. J.; Gregory Reid, J.; Myers, A. G.; Hahl, R. W. J. Am. Chem. Soc. 1987, 109, 918-919.
|
| [6] |
Schuster, H.; Martinez, R.; Bruss, H.; Antonchick, A. P.; Kaiser, M.; Schürmann, M.; Waldmann, H. Chem. Commun. 2011, 47, 6545-6547.
|
| [7] |
Kavitha, K.; Vidya, Priyadarsini R.; Anitha, P.; Ramalingam, K.; Sakthivel, R.; Purushothaman, G.; Singh, A. K.; Karunagaran, D.; Nagini, S. Eur. J. Pharmacol. 2012, 681, 6-14.
|
| [8] |
Roy, A.; Saraf, S. Biol. Pharm. Bull. 2006, 29, 191-201.
|
| [9] |
Nakatani, M. In Bioactive Compounds from Natural Sources, ed. C. Tringali, Taylor & Francis, London, U.K., 2001, ch. 13, pp. 527-554.
|
| [10] |
Wijeratne, E. M. K.; Bandara, B. M. R.; Gunatilaka, A. A. L.; Tezuka Y.; Kikuchi, T. J. Nat. Prod. 1992, 55, 1261-1269.
|
| [11] |
Editorial Committee (over 300 members) of the Administration Bureau of Traditional Chinese Medicine. In Chinese Materia Medica (Zhonghua Benchao); Shanghai Science & Technology Press:Shanghai, 1998; Vol. 5, pp 32-33.
|
| [12] |
Bandi, A. K.; Lee, D. U. Chem. Biodivers. 2012, 9, 1403-1421.
|
| [13] |
Chen, X. L.; Liu, H. L.; Guo, Y. W. Planta Med. 2012, 78, 286-290.
|
| [14] |
Wang, J. R.; Liu. H. L.; Kurtan, T.; Mandi, A.; Antus, S.; Li, J.;Zhang, H. Y.; Guo, Y. W. Org. Biomol. Chem. 2011, 26, 7685-7696.
|
| [15] |
Chen, X. L.; Liu, H. L.; Li, J.; Xin, G. R.; Guo, Y. W. Org. Lett. 2011, 13, 5032-5035.
|
| [16] |
Wang, J. R.; Kurtan, T.; Mandi, A.; Guo, Y W. Eur. J. Org. Chem. 2012, 5471-5482.
|
| [17] |
Li, Z. Y.; Chen, P.; Xu, H. G.; Yang, Y. M.; Peng, S. Y.; Zhao, Z. Z.; Guo, Y. W. Org. Lett. 2007, 9, 477-480.
|
| [18] |
Di, Y. T.; He, H. P.; Liu, H. Y.; Yi, P.; Zhang, Z.; Ren, Y. L.; Wang, J. S.; Sun, Q. Y.; Yang, F. M.; Fang, X.; Li, S. L.; Zhua, H. J.; Hao, X. J. J. Nat. Prod. 2007, 70, 1352-1355.
|
| [19] |
Wang, X. N.; Yin, S.; Fan, C. Q.; Lin, L. P.; Ding, J.; Yue, J. M. Tetrahedron 2007, 63, 8234-8241.
|
| [20] |
Venkatanarasimhan, M.; Kundu, A. B.; Patra, A. Indian J. Chem. 1978, 29B, 970.
|
| [21] |
Jiang, C. S.; Huang, C. G.; Feng, B.; Li, J.; Gong, J. X.; Kurtan, T.; Guo, Y. W. Steroids 2010, 75, 1153-1163.
|
|
Viewed |
|
|
|
Full text
|
|
|
|
|
Abstract
|
|
|
|
|
Cited |
|
|
|
|
| |
Shared |
|
|
|
|
| |
Discussed |
|
|
|
|
